5-(3-Benzyloxyphenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine → 5-(3-Hydroxyphenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo-[2,3-d]pyrimidine

HRID 362311Notes

Reaction equation

HRID 362311 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[N:17]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][N:34]4[CH:38]=[CH:37][N:36]=[CH:35]4)[CH:26]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>C1COCC1.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[N:17]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][N:34]4[CH:38]=[CH:37][N:36]=[CH:35]4)[CH:26]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 541929665-(3-Benzyloxyphenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 542304175-(3-Hydroxyphenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo-[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.85 g of 5-(3-benzyloxyphenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]-pyrimidine are hydrogenated in a hydrogen atmosphere at normal pressure and about 40° C. for 80 h in 40 ml of THF in the presence of 0.4 g of 5% palladium/carbon. After filtration through Celite and crystallization from ethanol, 5-(3-hydroxyphenyl)-7-[3-(2-(1-imidazolyl)-ethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine having a melting point of 165°-167° C. is obtained.

Workup

  1. filtrationAfter filtration
  2. customthrough Celite and crystallization from ethanol, 5-(3-hydroxyphenyl)-7-[3-(2-(1-imidazolyl)-ethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine having a melting point of 165°-167° C.
  3. customis obtained

Sources & evidence

ORD record
ord-d3df1d5d6b3e4c698aa09c69019031aa
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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